Triethylamine → HCID 19905465, compound

HRID 2371959Notes

Reaction equation

HRID 2371959 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH2:15][C:16]([OH:18])=O)=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.C(N(CC)CC)C.CC(C)(C)C(Cl)=O.Cl.[CH3:34][NH:35][OH:36]>ClCCl>[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH2:15][C:16]([N:35]([OH:36])[CH3:34])=[O:18])=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 62493Pivaloyl chlorideHCID 77906N-methylhydroxylamine hydrochlorideHCID 767163{[4-(2,5-Dimethyl-1H-pyrrol-1-yl)phenyl]sulfanyl}acetic acid

Product 1

HCID 19905465HCID 19905465, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g of 2-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-phenylthio]-acetic acid in 75 ml of dichloromethane and 0.8 ml. triethylamine, is cooled in an ice bath. To this solution is added 0.5 ml of trimethylacetyl chloride and the solution is stirred at room temperature overnight. Triethylamine (2 ml) is added followed by 1 g of N-methylhydroxylamine hydrochloride and the mixture is kept at room temperature for 20 hours. The mixture is washed with 0.3 N aqueous hydrochloric acid, ice cold dilute sodium bicarbonate and brine. The organic phase is dried over MgSO4 and filtered. The solvent is evaporated at 50° at reduced pressure, the residue is dissolved in diethyl ether and the solutions filtered through 10 g of silica gel to yield 2-[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenylthio]-N-hydroxy-N-methylacetamide; NMR (DMSO-d6 : δ7.1, 5.85, 3.25, 1.95.

Workup

  1. waitthe mixture is kept at room temperature for 20 hours
  2. washThe mixture is washed with 0.3 N aqueous hydrochloric acid, ice cold dilute sodium bicarbonate and brine
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customThe solvent is evaporated at 50° at reduced pressure
  6. dissolutionthe residue is dissolved in diethyl ether
  7. filtrationthe solutions filtered through 10 g of silica gel

Sources & evidence

ORD record
ord-29814b6a879549f589edf387aeb92f08
Source dataset
uspto-grants-1992_03
Patent number
US05096919

Reaction notes

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